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Street Art in Clarion Alley, San Francisco

When I started writing on the Keen IO blog in 2012, it opened it up a whole new world to me. One of my posts was published in an O’Reilly book. Another became part of the entrepreneurship curriculum at Harvard Business School, where I was invited to guest lecture. Several of my posts got 50k+ views. Suddenly, people I met in San Francisco already “knew” me from the blog. Folks wrote me personal emails asking for career advice. Werner Vogels, the CTO of amazon, retweeted one of my pieces to his 65,000 followers. It was incredibly rewarding.

Then… something changed.

When our company scaled from 8 people to 15, I started a draft about how hard that was, and what worked, and what didn’t. After several weeks, half of those ideas were already being disproven. We were going so fast. Defeated, I abandoned the draft and stopped blogging completely. That was a year ago.

But, looking back, it wasn’t my writing that was blocked, it was the sharing that I’d stopped doing.

In fact, after a 10+ years hiatus, I’d started writing letters again, to my now-pregnant childhood friend, back home in Illinois. Writing to her is as effortless as talking.

I told my friend about all the biggest things that were going in my life, which to be honest were 99% company-related. I told her about the teammate we knew we needed to let go, and how we were too chicken to do it. I told her about raising our Series A funding, and my mixed feelings about what that meant to me and my husband, and our company. I confessed about how surprisingly intimate it can be to work closely with people you trust & admire, and how confusing those feelings can be sometimes.

When she told me about how she was finally getting over morning sickness, I told her I couldn’t *think* about having kids anymore, because I was completely emotionally maxed out. By that point the company was 30 people and I felt personally responsible for all of them. That letter is where I finally admitted to myself how ridiculously I’d over-extended myself. It was such a relief.

When I look back, I’ve learned so much over the last year, and have a lot of regrets about not publishing any of it.

The truth of the matter is, I am terrified of sharing any of this type of stuff publicly. It’s a mix of Imposter Syndrome and outright Fear.

Here are some examples of thoughts I have:

  • Why would anyone care about what you have to say? Your story isn’t special. Keep your ego in check.
  • Your writing is mediocre at best. You just got lucky in the past because your friends up-voted your posts on Hacker News.
  • Our company has a brand now. That some people actually know about. Don’t screw it up.
  • The only reason people liked your posts was because you are a female and they were trying to be nice.
  • People already think the only reason you have this job is because your husband is the CEO. Blabbing about stuff you don’t really know that much about on the internet is not going to help your case.
  • If you write about your company, your friends and family back home are going to think you’re bragging about your success.

Taken one by one, these doubts are pretty easy to argue against, but the combination of them can feel like quicksand. With practice, we can all learn to quiet these voices, but it takes hard work.

Then there’s the straight-up Actual Risks category of anxieties. This is a special category that disproportionately affects women & minorities in the tech community. It’s the threat of the trolls, the misogynists, the racists, the rape threats. It’s accidentally getting your company DDOS’d because you complained at a conference. It’s the stalker-fan who sends you explicit messages through every channel, and knowing there’s nothing you can do about it except hope they don’t show up on your doorstep. This special kind of fear is a topic for entirely separate article, but I wanted to mention it briefly because it is a very real and true blocker for so many of us, particularly women in technology.

DESPITE all these doubts & fears. I still think it’s worth it to write.

So, this is me reminding myself:

  • of all the helpful posts I’ve read and how glad I am that people shared them. To pay it forward.
  • of the thank you notes and tweets I’ve gotten, for the stuff I wrote that really helped people.
  • that unlike a lot of other types of work, content keeps on giving long after you’ve published it, and it always seems worth it in hindsight
  • that I have a responsibility to the tech community. to do my part so that it’s not only men’s voices talking about technology and entrepreneurship.
  • that publishing has been some of the most rewarding work I have done in my career, and that it’s incredibly fulfilling. that doing it for myself might be reason enough.

Peace & Love,


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